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enReaction Design & OptimizationAsymmetric Reduction of Ketones

Asymmetric Reduction of Ketones

The enantioselective reduction of ketones to alcohols gives access to a pool of chiral building blocks that can be used for the synthesis of natural products. Adolfsson and co-workers reported a novel class of ligands, based on a pseudo-dipeptide,1 for the mild and efficient reduction of ketones using 2-propanol as a hydrogen source. The ligand is used with [{RuCl2(p-cymene)}2] in presence of NaOH for the asymmetric reduction of a variety of acetophenone derivatives. Excellent yields and ee’s were reported (Scheme 1).

Asymmetric Reduction of Ketones

Scheme 1.

Materials

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References

1.
Bøgevig A, Pastor IM, Adolfsson H. 2004. Highly Enantioselective Ruthenium-Catalyzed Reduction of Ketones Employing Readily Available Peptide Ligands. Chem. Eur. J.. 10(1):294-302. https://doi.org/10.1002/chem.200305553
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